Every so often, an evening unfolds in a way that feels deeply personal—less like dining out and more like stepping into someone else’s story. On a late spring night that felt suspiciously like peak summer, Winnipeg was showing off. Patios were full, drinks were cold, and the city’s golden-hour glow seemed determined to linger a little longer than usual. Tucked away on Osborne Street, inside Shirley’s, another kind of warmth was taking shape.

Guests gathered for the inaugural dinner of Air Canada’s Best New Restaurants Dining Series, presented in partnership with DINR. Hosted by Shirley’s and BabyBaby—neighbouring restaurants and finalists on the 2025 Air Canada’s Best New Restaurants list—it quickly became clear that the evening would be defined less by accolades than by hospitality.

There was a quiet electricity in the room, the kind that exists in the final moments before guests arrive, when every detail is finding its place. Small whimsical florals were being adjusted, and welcome pours of wine chilled to perfection. Staff moved with the calm confidence of people who knew exactly what kind of evening they were about to create. The feeling was familiar: equal parts excitement and nervous anticipation, like preparing to host a dinner party in your own home. Ali Vadeli, General Manager of Shirley’s, was the first to introduce herself, followed shortly after by Chef Renée Girard.

Along one wall, shelves stretched nearly floor to ceiling, lined with colourful jars of preserved beets, pickles, and root vegetables—both practical and beautiful, a reminder that great hospitality often lives in the details. For Chef Renée Girard, Shirley’s is a deeply rooted personal expression. Named after her grandmother, Shirley, the restaurant carries the same values that shaped the evening itself: generosity, familiarity, and the belief that food has a remarkable ability to bring people together. (I briefly considered whether I’d packed a large enough suitcase for the trip home—surely the Air Canada counter would understand a few extra pounds if they happened to be carrying jars of exceptionally good pickles.)

Nearby, Taylor from Element Wines guided guests through glasses of perfectly chilled sparkling white from Spain—light, refreshing, low in alcohol, and wonderfully drinkable. Out on Shirley’s back patio, guests gathered between conversations and canapés, many with a Shirley’s cocktail in hand, a combination of yuzu, pear, and prosecco that felt tailor-made for the occasion and the weather.

While guests settled in, I wandered next door to BabyBaby for a glimpse into the kitchen, camera in hand. Chef Chris Gama was putting the finishing touches on the “Chicken and Waffles.” Naturally, I was expecting fried chicken. Instead, perched atop a small slice of homemade waffle sat a rich chicken liver mousse, impossibly silky and deeply savoury—familiar in concept, entirely unexpected in execution. As I photographed the dish, Chef Chris and I shared a laugh about the prevalence of chef hands in close-up food photography, joking that perhaps the abundance of arm tattoos among chefs wasn’t entirely accidental—another excuse for a little personality to find its way into the frame. Looking back, the Chicken and Waffles remained one of the standout bites of the night. And it was just a “snack.”

As the top of the hour approached, guests began making their way next door to BabyBaby. The transition happened so naturally it was almost imperceptible—less like moving between restaurants and more like drifting from one room of the same house into another. Inside, BabyBaby glowed with intention. Rich dark wood anchored the room while vibrant colours softened it; a pink painted serpent stretched through the main corridor, quietly watching over the evening’s proceedings. Rosé was refreshed, martinis appeared, and guests settled into the comfortable rhythm that only great dinner parties seem capable of achieving.

Among the first stories shared at the table was a celebration of Prince Edward Island seafood alongside several BabyBaby signatures, including house-made sour cream and onion chips and their beloved Golden Eye dip from Gimli Fish Market. Elsewhere, Winnipeg’s iconic fergasa bread, baked in-house, arrived with a generous quenelle of whipped Notre Dame butter. For the unfamiliar, Winnipeg’s rye culture borders on civic pride—and one bite was enough to understand why. Dense yet delicate, earthy yet slightly sweet, it was the kind of bread that makes you question proportions entirely. I couldn’t decide whether I wanted butter with my bread or bread with my butter.

What has stayed with me most, though, wasn’t a particular dish. It was the way the chefs moved through the room. Renée, Nick, and Chris seemed to spend as much time among guests as they did in the kitchen. Plates rarely arrived without a story attached—one moment a producer, the next a childhood memory, a beloved Winnipeg institution, a family tradition. Somewhere along the way, the menu became a conversation. There was an unmistakable energy that followed the chefs all evening—not the energy of service, but of creation. The kind that appears when talented people are given permission to colour outside the lines.

Collaborations occupy a unique space in restaurant culture. Menus are, by necessity, finite things—defined, refined, repeated. Nights like this offer something different: a chance to wander, to revisit old ideas, test new ones, and pursue the creative impulses that might otherwise live only in notebooks and late-night conversations. Watching Renée, Nick, and Chris share those ideas—especially given that they spend their days cooking just steps from one another—felt like witnessing a conversation years in the making finally make its way onto the plate.

The salads carried that spirit beautifully. Shirley’s aptly named Very Nice Salad was, in fact, very nice—bright, tangy, lightly sweet, layered with texture from nuts, dried fruits, and crisp greens. BabyBaby’s cucumber and labneh salad offered a cooling counterpoint with a gentle spark of heat. But the dish that lingers longest was the ravioli doppio. Winnipeg’s Ukrainian influence runs deep, and nowhere was that heritage more beautifully expressed: one side an unmistakably Ukrainian interpretation of the Italian classic, filled with smoky kolbasa; the other faithful to tradition, rich with cheese. Together they floated in a broth so expressive it felt equally suited to a snowy prairie evening and the peak-summer warmth we were enjoying. Comfort without heaviness. Nostalgia without sentimentality.

If the ravioli was the evening’s emotional centrepiece, the ribeye was pure generosity. Sliced thin and arranged for sharing, cooked to a perfect medium rare, it needed very little embellishment. The servers thoughtfully delivered spoons alongside the steak knives—a decision that made immediate sense after the first bite, the jus rich and concentrated enough to invite appreciation right down to the final spoonful. As dinner settled into its final chapters, nobody seemed eager for it to end. A digestif built around a house-made banana schnapps arrived first—dessert in a glass—paired with an elevated take on Winnipeg’s Jeanne’s Cake and capped with the LA Squishy, effectively an adult float that brought both nostalgia and whimsy.

Great restaurants have an uncanny ability to follow us home. For me, it was Shirley’s famous Black Market Crunch, which each of us was lucky enough to take home—a true extension of the evening that I still reach for today. A spoonful folded into morning eggs. A generous scatter over a summer burger. A conversation starter at a dinner party weeks later. Long after the flight home—a journey that required enough commitment to this little jar that my carry-on became a checked suitcase—it still sits quietly in the cupboard. All it takes is twisting off the lid to revisit a particular room, a particular city, a particular evening. Perhaps that’s why Winnipeg felt like such a fitting place to begin this new series: welcoming, generous, and rich with stories waiting to be shared. If the energy in the room was any indication, everyone left hoping this would be the first of many chapters still to come.